CA2200700C - Catalyzed vapor phase hydrocyanation of diolefinic compounds - Google Patents

Catalyzed vapor phase hydrocyanation of diolefinic compounds Download PDF

Info

Publication number: CA2200700C
Authority: CA; Canada
Prior art keywords: reaction; hcn; catalyst; diolefinic; butadiene
Prior art date: 1994-11-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002200700A

Other languages

English (en)

French (fr)

Other versions

CA2200700A1 (en

Inventor

Joe Douglas Druliner

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

INVISTA TECHNOLOGIES Sarl

Original Assignee

INVISTA TECHNOLOGIES Sarl

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-11-18

Filing date

1995-11-01

Publication date

2007-01-09

1995-11-01 Application filed by INVISTA TECHNOLOGIES Sarl filed Critical INVISTA TECHNOLOGIES Sarl

1996-05-30 Publication of CA2200700A1 publication Critical patent/CA2200700A1/en

2007-01-09 Application granted granted Critical

2007-01-09 Publication of CA2200700C publication Critical patent/CA2200700C/en

2015-11-01 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 34
238000005669 hydrocyanation reaction Methods 0.000 title claims abstract description 20
239000012808 vapor phase Substances 0.000 title abstract description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 44
239000003054 catalyst Substances 0.000 claims abstract description 33
238000000034 method Methods 0.000 claims abstract description 28
239000003446 ligand Substances 0.000 claims abstract description 26
230000008569 process Effects 0.000 claims abstract description 26
229910052759 nickel Inorganic materials 0.000 claims abstract description 12
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
125000002015 acyclic group Chemical group 0.000 claims abstract description 3
150000002825 nitriles Chemical class 0.000 claims abstract 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 45
238000006243 chemical reaction Methods 0.000 claims description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229930195733 hydrocarbon Natural products 0.000 claims description 5
150000002430 hydrocarbons Chemical group 0.000 claims description 5
239000000377 silicon dioxide Substances 0.000 claims description 5
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000001993 dienes Chemical class 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
238000010923 batch production Methods 0.000 claims 1
238000010924 continuous production Methods 0.000 claims 1
CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
238000004817 gas chromatography Methods 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000007789 gas Substances 0.000 description 16
239000012071 phase Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 8
WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000005977 Ethylene Substances 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
230000004044 response Effects 0.000 description 6
-1 acyclic nitrites Chemical class 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 5
SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 4
KOVZMYUXIJOHCD-UHFFFAOYSA-N 2-methyloctanenitrile Chemical compound CCCCCCC(C)C#N KOVZMYUXIJOHCD-UHFFFAOYSA-N 0.000 description 4
239000011261 inert gas Substances 0.000 description 4
239000000376 reactant Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
PLZZPPHAMDJOSR-UHFFFAOYSA-N nonanenitrile Chemical compound CCCCCCCCC#N PLZZPPHAMDJOSR-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
241000156948 Aphantopus hyperantus Species 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CXQXWHWPDDUDPI-UHFFFAOYSA-N [Cu+2].[Zn+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O Chemical compound [Cu+2].[Zn+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O CXQXWHWPDDUDPI-UHFFFAOYSA-N 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
NKKMVIVFRUYPLQ-UHFFFAOYSA-N but-2-enenitrile Chemical compound CC=CC#N NKKMVIVFRUYPLQ-UHFFFAOYSA-N 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
241000894007 species Species 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000009834 vaporization Methods 0.000 description 2
230000008016 vaporization Effects 0.000 description 2
239000002699 waste material Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
RHQKKJPJCHGKQO-UHFFFAOYSA-N [Cu+2].[O-][Cr]([O-])=O Chemical class [Cu+2].[O-][Cr]([O-])=O RHQKKJPJCHGKQO-UHFFFAOYSA-N 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000010949 copper Substances 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
238000007210 heterogeneous catalysis Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(II) nitrate Inorganic materials [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000005070 sampling Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
- C07C255/07—Mononitriles
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Inorganic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Toxicology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA002200700A 1994-11-18 1995-11-01 Catalyzed vapor phase hydrocyanation of diolefinic compounds Expired - Fee Related CA2200700C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/342,195 US5449807A (en)	1994-11-18	1994-11-18	Catalyzed vapor phase hydrocyanation of diolefinic compounds
US08/342,195		1994-11-18
PCT/US1995/014787 WO1996016022A1 (en)	1994-11-18	1995-11-01	Catalyzed vapor phase hydrocyanation of diolefinic compounds

Publications (2)

Publication Number	Publication Date
CA2200700A1 CA2200700A1 (en)	1996-05-30
CA2200700C true CA2200700C (en)	2007-01-09

Family

ID=23340777

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002200700A Expired - Fee Related CA2200700C (en)	1994-11-18	1995-11-01	Catalyzed vapor phase hydrocyanation of diolefinic compounds

Country Status (12)

Country	Link
US (1)	US5449807A (de)
EP (1)	EP0792259B1 (de)
JP (1)	JP3478399B2 (de)
KR (1)	KR100252616B1 (de)
CN (1)	CN1068307C (de)
AT (1)	ATE182881T1 (de)
BR (1)	BR9510347A (de)
CA (1)	CA2200700C (de)
DE (1)	DE69511284T2 (de)
ES (1)	ES2138761T3 (de)
MY (1)	MY115991A (de)
WO (1)	WO1996016022A1 (de)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2177135C (en) *	1993-11-23	2005-04-26	Wilson Tam	Processes and catalyst compositions for hydrocyanation of monoolefins
BR9507460A (pt)	1994-04-14	1997-09-02	Du Pont	Processo para hidrocianação e composição de precursor de catalisador
US5512695A (en) *	1994-04-14	1996-04-30	E. I. Du Pont De Nemours And Company	Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins
US5512696A (en) *	1995-07-21	1996-04-30	E. I. Du Pont De Nemours And Company	Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor
TW315370B (de) *	1994-10-07	1997-09-11	Du Pont
IN187044B (de) *	1995-01-27	2002-01-05	Du Pont
US5821378A (en) *	1995-01-27	1998-10-13	E. I. Du Pont De Nemours And Company	Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles
EP1621531B1 (de) *	1996-04-02	2007-03-14	INVISTA Technologies S.à.r.l.	Katalysierte Gasphasen-Addition von Cyanwasserstoff an Diolefine
IN191521B (de) *	1996-04-02	2003-12-06	Du Pont
DE19652273A1 (de) *	1996-12-16	1998-06-18	Basf Ag	Monoolefinische C¶5¶-Mononitrile, Verfahren zu ihrer Herstellung und ihre Verwendung
ZA986369B (en) *	1997-07-29	2000-01-17	Du Pont	Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles.
US6121184A (en) *	1997-07-29	2000-09-19	E. I. Du Pont De Nemours And Company	Supported bis(phosphorus) ligands
DE19825212A1 (de)	1998-06-05	1999-12-09	Basf Ag	Katalysator, umfassend einen Komplex eines Metalls der VIII. Nebengruppe auf Basis eines zweizähnigen Phosphonitliganden und Verfahren zur Herstellung von Nitrilen
BR0014567A (pt)	1999-09-20	2002-06-18	Du Pont	Processo de hidrocianação, ligante de fosfito multidentado e composição de catalisador
US6515161B1 (en)	1999-09-20	2003-02-04	E. I. Du Pont De Nemours And Company	Hydroformylation process utilizing multidentate phosphite ligands
US6753440B2 (en) *	2001-05-11	2004-06-22	E.I. Du Pont De Nemours And Company	Copper-catalyzed vapor phase hydrocyanation of diolefinic compounds
FR2850966B1 (fr)	2003-02-10	2005-03-18	Rhodia Polyamide Intermediates	Procede de fabrication de composes dinitriles
FR2854891B1 (fr)	2003-05-12	2006-07-07	Rhodia Polyamide Intermediates	Procede de preparation de dinitriles
FR2854892B1 (fr)	2003-05-12	2005-06-24	Rhodia Polyamide Intermediates	Procede de fabrication de dinitriles
ES2532982T3 (es)	2005-10-18	2015-04-06	Invista Technologies S.À.R.L.	Proceso de preparación de 3-aminopentanonitrilo
WO2007109005A2 (en)	2006-03-17	2007-09-27	Invista Technologies S.A R.L.	Method for the purification of triorganophosphites by treatment with a basic additive
US7709674B2 (en)	2006-07-14	2010-05-04	Invista North America S.A R.L	Hydrocyanation process with reduced yield losses
US7919646B2 (en)	2006-07-14	2011-04-05	Invista North America S.A R.L.	Hydrocyanation of 2-pentenenitrile
US7880028B2 (en)	2006-07-14	2011-02-01	Invista North America S.A R.L.	Process for making 3-pentenenitrile by hydrocyanation of butadiene
EP2146930A2 (de)	2007-05-14	2010-01-27	INVISTA Technologies S.à.r.l.	Hocheffizienter reaktor und entsprechendes verfahren
WO2008157218A1 (en)	2007-06-13	2008-12-24	Invista Technologies S.A.R.L.	Process for improving adiponitrile quality
CN101918356B (zh)	2008-01-15	2013-09-25	因温斯特技术公司	戊烯腈的氢氰化
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1994
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1995
- 1995-10-31 MY MYPI9503285 patent/MY115991A/en unknown
- 1995-11-01 KR KR1019970703331A patent/KR100252616B1/ko not_active Expired - Fee Related
- 1995-11-01 BR BR9510347A patent/BR9510347A/pt not_active IP Right Cessation
- 1995-11-01 AT AT95941390T patent/ATE182881T1/de not_active IP Right Cessation
- 1995-11-01 CN CN95196276A patent/CN1068307C/zh not_active Expired - Lifetime
- 1995-11-01 CA CA002200700A patent/CA2200700C/en not_active Expired - Fee Related
- 1995-11-01 JP JP51695296A patent/JP3478399B2/ja not_active Expired - Fee Related
- 1995-11-01 ES ES95941390T patent/ES2138761T3/es not_active Expired - Lifetime
- 1995-11-01 WO PCT/US1995/014787 patent/WO1996016022A1/en not_active Ceased
- 1995-11-01 EP EP95941390A patent/EP0792259B1/de not_active Expired - Lifetime
- 1995-11-01 DE DE69511284T patent/DE69511284T2/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
WO1996016022A1 (en)	1996-05-30
CN1163606A (zh)	1997-10-29
BR9510347A (pt)	1997-12-23
KR970707078A (ko)	1997-12-01
EP0792259A1 (de)	1997-09-03
JP3478399B2 (ja)	2003-12-15
ES2138761T3 (es)	2000-01-16
MY115991A (en)	2003-10-31
EP0792259B1 (de)	1999-08-04
KR100252616B1 (ko)	2000-04-15
CN1068307C (zh)	2001-07-11
JPH10509954A (ja)	1998-09-29
DE69511284D1 (de)	1999-09-09
ATE182881T1 (de)	1999-08-15
DE69511284T2 (de)	2000-04-06
US5449807A (en)	1995-09-12
CA2200700A1 (en)	1996-05-30

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Publication	Publication Date	Title
CA2200700C (en)	2007-01-09	Catalyzed vapor phase hydrocyanation of diolefinic compounds
EP1000020B1 (de)	2003-04-09	Hydrocyanierung von diolefinen und isomierung von nicht-konjugierten 2-alkyl-3-monoalkennitrilen
EP1000021B1 (de)	2002-10-02	Cyanwasserstoffaddition an diolefine und isomierung von nicht konjugierten 2-alkyl-3-monoalkennitrilen
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US6753440B2 (en)	2004-06-22	Copper-catalyzed vapor phase hydrocyanation of diolefinic compounds
WO2003076394A1 (en)	2003-09-18	Phosphonite ligands and their use in hydrocyanation
EP0891323B1 (de)	2006-06-14	Katalysierte gasphasen-addition von cyanwasserstoff an diolefine
EP1621531B1 (de)	2007-03-14	Katalysierte Gasphasen-Addition von Cyanwasserstoff an Diolefine
EP0891324B1 (de)	2001-09-12	Katalysierte gasphasenisomerisierung von nicht konjugierten 2-alkyl-3-monoalkennitrilen